Porphyrazine with bulky 2-(1-adamantyl)-5-phenylpyrrol-1-yl periphery tuning its spectral and electrochemical properties

The synthesis and physicochemical properties of a novel porphyrazine possessing an alternate system of two peripheral substituents, 2-(1-adamantyl)-5-phenylpyrrol-1-yl and dimethylamino, are presented. Precursor maleonitriles were characterized using X-ray crystallography. Novel porphyrazine was subjected to spectroscopic studies, including the determination of fluorescence quantum yield and singlet oxygen quantum yield. Moreover, its electrochemical and spectroelectrochemical properties were investigated. The antimicrobial photodynamic activities of the novel porphyrazine encapsulated in various liposomal formulations were tested against Staphylococcus aureus and Pseudomonas aeruginosa.

Graphical abstractThe synthesis and physicochemical properties of a novel porphyrazine possessing 2-(1-adamantyl)-5-phenylpyrrol-1-yl and dimethylamino groups as substituents, are presented. Spectroscopic studies, including the determination of fluorescence quantum yield and singlet oxygen quantum yield were conducted. Moreover, electrochemical and spectroelectrochemical properties of the porphyrazine were investigated.Figure optionsDownload full-size imageDownload as PowerPoint slide